HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 15907678, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Reactant | (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid | HCID 15887219 | — |
| Reactant | 7-Azabicyclo[2.2.1]heptane hydrochloride | HCID 16279503 | — |
| Reactant | Sodium chloride dihydrate | HCID 23713072 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 15907678 | HCID 15907678 | 94.4% |
Reaction Steps
PyBOP (1.51 g, 2.89 mmol) was added to a stirred mixture of the crude (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid (1.20 g, 2.63 mmol), 7-azabicyclo[2.2.1]heptane hydrochloride (0.70 g, 5.26 mmol) and triethylamine (1.47 mL, 10.5 mmol) in dichloromethane (26 mL) at ambient temperature. After approximately 12h, the reaction mixture was poured into water/brine (1:1) and extracted with ethyl acetate (x3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (gradient eluton; 60-75% ethyl acetatethexanes as eluent) to give the title compound as a foam (1.33 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06228867B1 |
| Source dataset | uspto-grants-2001_05 |
| ORD ID | ord-adb096e7f5d046bcba1b1ba39f6ec5ff |
| Source note | uspto-grants-2001_05 |